Everyone knows AI can do magical things. We also all know that sometimes it’s not quite as magical as we want it to be. Over the past few weeks, I’ve been testing out the latest wave of AI tools, especially the ones used for video. And in the midst of this, this ad from Kalshi caught my eye. Watch this: Kalshi @Kalshi History was made by the underdogs. 9:0 AM • Jul 10, 2025 434 Retweets 3311 Likes Read 263 replies The entire video is AI generated...sort of. Each clip was generated using...
about 1 month ago • 2 min read
Sinner and Świątek are the official winners of Wimbledon, but the unofficial winners? Their social team. If you were on TikTok or Instagram during the tournament, you might have seen a clip that went viral. Not of a highlight reel or championship point, but of two people in the crowd debating a player’s age. “He must be pushing 40.” “No, he's 38.” “Why, that would be pushing 40!” That’s from a series Wimbledon ran called Overheard at Wimbledon. It's a simple concept where they mic up willing...
about 2 months ago • 1 min read
While CMOs argue about whether they should even be on an app “for teenage girls doing dances,” a much bigger shift is happening. Namely, Tiktok is evolving from a feed-based app to a search-driven platform. That changes how content gets discovered, how brands get found, and how you win. I was recently in Cannes and saw this ad at the airport: It’s subtle, but it signals a major shift in how TikTok is positioning itself. Not just as entertainment, but as the go-to destination for discovery and...
about 2 months ago • 3 min read
This week, we're highlighting Red Lobster and how their new CEO, Damola Adamolekun, is making waves simply by speaking strategy out loud on social. Check out this clip to see what I mean: The Breakfast Club As the new CEO of @redlobster, Damola Adamolekun dives into his plan to save the company from Chapter 11 by tapping into the brand's nostalgia and rebranding! 🦞#iHEARTRADIO ♬ original sound - The Breakfast Club - The Breakfast Club At a time when most brands are chasing attention with...
2 months ago • 2 min read
Not every founder or brand wants to churn out content 24/7, but in 2025 it feels like you have no choice. Today let’s break down why that is, and what the alternatives actually are. Here’s a video I saw this week from the owner of a beauty brand voicing this frustration: https://www.instagram.com/p/DKSzH4LyL4J/ 1. Why do we even have to create? As someone who often talks about the benefit of creating content, it comes down to this: when done well, it creates outsized awareness, attention, and...
2 months ago • 2 min read
Quick follow-up on last week's Waterboy breakdown: someone reminded me of an obvious, but important point I always say organic social is one of the higher leverage channels and "free" to get reach, but the true cost is the time spent to create the content and maintain presence on the channel. And in Waterboy's case, actually sending people on the trip (though relative to the reach and conversation I'm sure it's a good return). Now for this week's breakdown. Why would a cosmetics company send...
3 months ago • 3 min read
A few weeks ago I made a video talking about why the traditional brand trip is "dead," so it was only fitting that this week I saw a video from Waterboy Hydration doing something completely different. Let's take a look: Waterboy WATERBOY BRAND TRIP 2.0 IN TULUM!!! We are taking 24 customers and creators to Tulum June 23-26 for the party of a lifetime and YOU can come by making a TikTok from now until April 25 using #WaterboyinTulum and tagging us 🏝️ The only rule is there are no rules - be...
3 months ago • 2 min read
For this week’s edition, I want to take a look at Ryan Serhant. If you don’t know him, he’s a NYC based real estate broker turned media mogul. Check out one of his recent videos: Ryan Serhant Real Estate Rapid Fires ♬ Make It Better (Instrumental) - Anderson .Paak For the past few years he's been building a media empire, and here's what I find working in some of his content: Turns "work" into content One of the reasons "behind the scenes" content works, is because 99.9% of people never get to...
3 months ago • 1 min read
I usually highlight great content from brands, but today I’m going to talk about what to avoid. Today’s unlucky subject is LIFEWTR (which, admittedly, is successful on its own and doesn’t need much of a social presence anyway). You can scroll through their account here: LIFEWTR Which LIFE is right for you? ♬ Forest, trees, nature, piano, cute pops(983271) - Gloveity They’re a good example of how large brands get social (and short form) wrong. Here are a few patterns and issues I see:...
4 months ago • 2 min read
